p-(Hexyloxy)benzaldehyde → HCID 21182493, compound

HRID 1386584Notes

Reaction equation

HRID 1386584 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[NH2:12])[C:5]([O:7][CH3:8])=[O:6].[CH2:13]([O:19][C:20]1[CH:27]=[CH:26][C:23]([CH:24]=O)=[CH:22][CH:21]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]>[N+](C1C=CC=CC=1)([O-])=O>[CH3:8][O:7][C:5]([C:4]1[CH:9]=[CH:10][C:11]2[N:12]=[C:24]([C:23]3[CH:26]=[CH:27][C:20]([O:19][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:21][CH:22]=3)[NH:1][C:2]=2[CH:3]=1)=[O:6]

Participants

4

Reactant 2

HCID 79816p-(Hexyloxy)benzaldehydeHCID 1355243,5-Diamino-2-methylbenzoic acid

Product 1

HCID 21182493HCID 21182493, compoundYield 48.9%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Conditions

Temperature
145 °C

Procedure

A mixture of Methyl 3,4-diaminobenzoate (1.84 g) and 4-hexyloxy benzaldehyde (2.30 g) in nitrobenzene (40 ml) was stirred for 48 hours at 145° C. After cooling, the mixture was evaporated under reduced pressure. Purification of the residue by column chromatography on silica gel eluted with (n-hexane:ethyl acetate=2:1) gave 5-Methoxycarbonyl-2-(4-hexyloxyphenyl)benzimidazole (1.91 g).

Workup

  1. temperatureAfter cooling
  2. customthe mixture was evaporated under reduced pressure
  3. customPurification of the residue by column chromatography on silica gel
  4. washeluted with (n-hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-43a621d41eaf4a6cb2bf2126aca2a486
Source dataset
uspto-grants-2001_07
Patent number
US06265536B1

Reaction notes

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